Ethylene sulphide reaction products of guanidine



Patented Mar. 27, 1945 ETHYLENE SULPHIDE REACTION PRODUCTS OF GUANIDINELeonard P. Moore, New York, N. Y., and Walter P. Ericks, Stamford,Conn., assignors to American Cyanamid Company, New York, N. Y., acorporation of Maine No Drawing. Application September 19, 1942, SerialNo. 459,000

1 Claim.

This invention relates to the preparation of new guanidine derivatives.More particularly it embraces the reaction of ethylene sulphide withguanidine. It relates especially to the preparation of mercapto-alkylguanidines. This case is a continuation-in-part of Serial No. 370,146,filed December 14, 1940, by Leonard P. Moore and Walter P. Ericks nowPatent 2,323,409.

It is an object of this invention to prepare these compounds by simpleand efiicient processes. A further object is to obtain them in aconveniently utilizable form. Other and further objects as well as usesfor the compounds herein prepared will be found in the followingdescription.

The objects of this invention are attained by reacting ethylene sulphidewith guanidine. These reactions may be effected with or without external heating or cooling.

The new preparations find a very wide range of uses. For example, theycan be applied to leather as dehairing agents. They are useful also asintermediates in the preparation of resins, some forming resinouspolymerization products by simply heating the product. Still others arehighly effective and cheap insecticides. Still other uses are found inthe compounding of rubber and rubber containin articles where theproducts of this invention are found to exert favorable plasticizing andsome vulcanization accelerating activity.

In order to facilitate a further understanding of the invention, thefollowing examples are given primarily for the purpose of illustratingcertain more specific details thereof. The scope of the invention is notto be deemed limited thereby except as defined in the claim.

Example 9 g. of guanidine carbonate (0.05 mol.) were dissolved in 100cc. of denatured ethyl alcohol containing 5.8 cc. of sulphuric acid (0.1mol.). 8.4 g. of sodium hydroxide (0.2 mol.) dissolved in 25 cc. ofwater was added and the precipitate of sodium sulphate formed wasseparated by filtration. The filtrate was evaporated to 20 cc. on asteam bath under vacuum. 6 g. of ethylene sulphide was added to thisaqueous solution, the reaction mixture refluxed for 3 hours and dried atC. to yield 11.4 g. of the desired product Z-mercaptoethyl guanidine.

It is to be understood that the scope of this invention is not to belimited by the examples specifically contained herein illustratingspecific embodiments of the invention since many modifications andvarious combining weights of the reacting ingredients may be used, butthat it is to be construed broadly and restricted solely by the scope ofthe appended claim.

We claim:

A method of preparing ethylene sulphideguanidine complexes whichcomprises reacting molecularly equivalent proportions of guanadinecarbonate and ethylene sulphide by effecting the reaction of theguanidine carbonate in an equeous alcoholic menstruum, acidified withsulphuric acid, the latter being neutralized with a substantiallyequivalent'reacting proportion of sodium hydroxide to form a precipitateof sodium sulphate, filtering out the precipitate and reacting thefiltrate with the reacting proportion of ethylene sulphide, andrefluxing.

LEONARD P. MOORE. WALTER P. ERICKS.

